Reacción #169569

Ecuación de reacción

H2O2

tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropylcarbamate

2,4-dimethoxybenzaldehyde

Na2SO3

→

(S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid

Rendimiento 94.2%

Disolventes

H2O

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to 0° C
2. 2
   workup.ADDITIONA solution containing
3. 3
   workup.ADDITIONwas added dropwise by addition funnel
4. 4
   OtroThe reaction mixture was placed in an ice bath
5. 5
   Temperaturato slowly warm the reaction mixture and it
6. 6
   workup.STIRRINGwas stirred overnight
7. 7
   TemperaturaThe reaction mixture was then cooled to 0° C.
8. 8
   workup.STIRRINGThe mixture was stirred for 5 minutes
9. 9
   Temperaturawarmed to room temperature
10. 10
    workup.STIRRINGwhile being stirred for 20 minutes
11. 11
    OtroThe reaction mixture was then transferred to a separatory funnel
12. 12
    Lavadowashed with ether (3×)
13. 13
    Extracciónthe mixture was extracted with DCM (2×)
14. 14
    SecadoThe combined extracts were dried (Na2SO4)
15. 15
    Filtraciónfiltered
16. 16
    Concentraciónconcentrated

Procedimiento

35% H2O2 (0.240 mL, 2.91 mmol) was added to a solution of LiO—H2O (0.0978 g, 2.33 mmol) in 2:1 THF:H2O (33 mL). The reaction mixture was stirred at room temperature for 35 minutes and then cooled to 0° C. A solution containing a mixture of tert-butyl (S)-3-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-(4-chlorophenyl)-3-oxopropylcarbamate (0.535 g, 1.17 mmol) and 2,4-dimethoxybenzaldehyde (0.194 g, 1.17 mmol) in THF (7 mL) was added dropwise by addition funnel. The reaction mixture was placed in an ice bath to slowly warm the reaction mixture and it was stirred overnight. The reaction mixture was then cooled to 0° C., and 1M Na2SO3 (7 mL) was added to the mixture. The mixture was stirred for 5 minutes and then warmed to room temperature while being stirred for 20 minutes. The reaction mixture was then transferred to a separatory funnel and washed with ether (3×). The aqueous layer was acidified with KHSO4(s), and the mixture was extracted with DCM (2×). The combined extracts were dried (Na2SO4), filtered, and concentrated to give (S)-3-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)propanoic acid (0.329 g, 94.2% yield) as a white residue. LC/MS (APCI+) m/z 200 [M−BOC+H]+.

Fuente